Pyridinium 1,1'-binaphthyl-2,2'-disulfonates as highly effective chiral Brønsted acid-base combined salt catalysts for enantioselective Mannich-type reaction

Manabu Hatano; Toshikatsu Maki; Katsuhiko Moriyama; Manabu Arinobe; Kazuaki Ishihara

doi:10.1021/ja806875c

Pyridinium 1,1'-binaphthyl-2,2'-disulfonates as highly effective chiral Brønsted acid-base combined salt catalysts for enantioselective Mannich-type reaction

J Am Chem Soc. 2008 Dec 17;130(50):16858-60. doi: 10.1021/ja806875c.

Authors

Manabu Hatano¹, Toshikatsu Maki, Katsuhiko Moriyama, Manabu Arinobe, Kazuaki Ishihara

Affiliation

¹ Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya, 464-8603, Japan.

PMID: 19053478
DOI: 10.1021/ja806875c

Abstract

We have established, for the first time, a practical synthesis of chiral 1,1'-binaphthyl-2,2'-disulfonic acid (BINSA 1) from inexpensive BINOL. An efficient enantioselective catalysis in the Mannich-type reactions of diketones and ketoester equivalents with aldimines was developed using chiral 1-achiral 2,6-diarylpyridine (2) combined salts, which acted as convenient chiral tailor-made Brønsted acid-base organocatalysts in situ.